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Can I piggyback on this question with a related margin interest issue? If I use margin to buy both stocks and options, but only sell the options for a profit while keeping the stocks, can I deduct all the margin interest? Or only the portion related to the options I sold?
You can deduct all your margin interest up to the amount of your total investment income, regardless of which specific securities you sold. The IRS doesn't require you to match interest expenses to specific securities or transactions. So if your options trading generated sufficient investment income to cover all your margin interest for the year (from both stocks and options), you can deduct the full amount of interest. Just make sure to complete Form 4952 correctly to calculate your allowable deduction.
Just wanted to add a practical tip from my experience with a similar situation. When you're preparing your taxes, make sure you have good documentation of all your margin interest payments throughout the year. Your brokerage should provide this on your 1099-INT or in your monthly statements, but it's worth double-checking the totals. Also, keep in mind that if you have multiple brokerage accounts, you'll need to aggregate all your investment income and all your investment interest expenses across all accounts when completing Form 4952. The IRS looks at your total investment picture, not account by account. One more thing - if you're planning to continue using margin in future years, consider keeping a spreadsheet to track your margin interest payments monthly. This makes tax prep much easier and helps you project whether you'll have enough investment income to fully deduct the interest each year.
Just wanted to mention that you can actually e-file past year returns using some tax software, which is WAY easier than paper filing. I used FreeTaxUSA for my 2020 return when I filed in late 2023. They charge like $20 for past year returns but it was totally worth it to avoid the paper forms nightmare.
I thought you could only e-file current year returns? Every time I've tried to do old returns the software always makes me print and mail them in.
@Malik Thompson is right - FreeTaxUSA does allow e-filing for prior years, but there are some limitations. You can typically e-file returns from the current year and the previous 3-4 years depending on the software. For 2020 returns filed in 2025, you might be past the e-file window for that specific year, but it s'worth checking since different software providers have different cutoff dates. TurboTax and H&R Block also offer prior year e-filing for a fee, usually around $50-80 per return.
I'm going through a very similar situation right now with my 2020 taxes! Lost my job in March 2020 and honestly just couldn't deal with paperwork for the longest time. I finally gathered all my documents last month and realized I might actually owe money despite having taxes withheld from my W-2. One thing that really helped me was calling the IRS Taxpayer Advocate Service (TAS) - they're a separate division that helps people with complex tax problems for free. They don't file your return for you, but they can explain your options and help you understand what penalties you might face. The number is 1-877-777-4778. They were way more patient and helpful than trying to navigate the regular IRS phone system. Also, don't panic about the penalties if you do owe. The failure-to-file penalty stops accruing after 5 months, so it maxes out at 25% of what you owe. The failure-to-pay penalty continues but it's only 0.5% per month. Still not great, but not as scary as it sounds when people say "penalties keep growing forever.
Thanks for sharing that TAS number! I've been putting this off for so long partly because I was terrified of dealing with the IRS directly. Knowing there's a separate service that's actually designed to help people like us is really reassuring. Did they give you specific guidance on how to calculate what you might owe, or did they mainly just explain the process? I'm still trying to figure out if my freelance expenses might offset some of that 1099 income before I panic about the penalties.
Does anyone know if the financial institution you transfer the inherited 401k to matters? I've heard some places handle stretch IRAs better than others since the SECURE Act changes. I'm in a similar situation where I qualify as an eligible designated beneficiary (I'm disabled) but worried about choosing the right place to transfer my late husband's 401k.
In my experience, the larger financial institutions like Fidelity, Vanguard, and Charles Schwab tend to be more knowledgeable about the SECURE Act provisions and have specific protocols for handling eligible designated beneficiaries. When I transferred my inherited account to Fidelity, they had a specialized team that handled these situations and knew exactly what documentation I needed. I'd avoid smaller local banks that might not deal with these situations regularly enough to be familiar with all the exceptions.
I'm dealing with a very similar situation and wanted to share what I learned from my estate attorney. Since you're older than the original 401k owner, you definitely qualify as an "eligible designated beneficiary" under the SECURE Act exception for individuals not more than 10 years younger than the decedent. One thing that hasn't been mentioned yet - make sure when you do the rollover that it's titled correctly as an "inherited IRA" with both your name and the deceased's name (something like "Kaitlyn Otto as beneficiary of [deceased's name] IRA"). This is crucial for maintaining the tax-deferred status and ensuring you can take the stretch distributions properly. Also, since the original owner passed in 2022, you should have already started taking RMDs by December 31, 2023. If you missed that deadline, you may need to file Form 5329 to request a waiver of the 50% penalty, but the IRS has been more lenient with inherited account penalties during the transition period after the SECURE Act. I'd strongly recommend getting everything documented before you approach the financial institution, because as others have mentioned, many of them are still learning these rules themselves.
This is incredibly helpful information about the account titling - I hadn't thought about that detail but it makes perfect sense that it needs to be set up as an inherited IRA with both names. Quick question about the missed RMD deadline: since I'm just now getting this sorted out in 2025, am I looking at penalties for both 2023 and 2024? And is Form 5329 something I can file myself or do I need professional help with that? The documentation point is well taken too. It sounds like I should go in armed with birth certificates, death certificate, IRS publications, and a clear explanation of which exception I fall under. Better to over-prepare than have to go back multiple times!
For anyone in this situation, please remember that if your income was only $14k in 2023, you were probably under the filing requirement threshold anyway! For 2023, single filers under 25 didn't need to file if they made less than $12,950.
That's not completely accurate. The standard deduction was $12,950 in 2023, but you could still be required to file depending on other factors like self-employment income (even small amounts), if someone claimed you as a dependent, or if you had health insurance through the marketplace.
Don't feel embarrassed at all - you're definitely not alone in this situation! I work as a tax preparer and see people in similar circumstances all the time. The good news is that with your income level of $14,000, you're almost certainly due a refund rather than owing anything. Here's what I'd recommend: First, gather your 2023 W-2 from the coffee shop (contact them if you can't find it - they're required to provide copies). Then you have a few options - you can use free tax software like the IRS Free File program, visit a VITA (Volunteer Income Tax Assistance) location for free help, or even just fill out a simple 1040 form. The key thing is that there's no penalty for filing late when you're due a refund. You have until April 15, 2027 to claim your 2023 refund, so you've got plenty of time. Once you file, you'll probably get back most or all of what was withheld from your paychecks, and you might even qualify for the Earned Income Tax Credit which could mean extra money back. You're taking the right step by asking for help - don't let tax anxiety keep you from claiming money that's rightfully yours!
Abigail bergen
One thing nobody has mentioned yet - beware of the "Currently Not Collectible" status these companies often push. It might sound great (the IRS agrees not to collect from you temporarily), but the 10-year clock keeps running AND interest and penalties keep accumulating! Sometimes it makes more sense to set up even a small payment plan to start chipping away at the debt. For 2012-2014, if you haven't filed yet, file ASAP. The assessment date (which starts the 10-year clock) begins when you file and the IRS processes your return. So those years aren't even on the clock yet. I'd recommend calling the IRS Taxpayer Advocate Service. They're independent from the IRS collection division and can give you free guidance. Their number is 877-777-4778.
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Ahooker-Equator
ā¢I tried calling the Taxpayer Advocate Service and was told they have a 6-8 week backlog for new cases unless you're literally about to be evicted or have your utilities shut off. Did you have better luck getting through to them?
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Aisha Abdullah
I'm dealing with a similar situation right now - owe about $28,000 for 2020-2022 and just got the levy notice last week. Reading through all these responses has been incredibly helpful, especially learning about the 10-year rule and how it actually works. I called one of those tax relief companies too and they wanted $3,200 upfront after a $500 "consultation fee." After reading everyone's experiences here, I'm definitely not going that route. Question for those who've been through this - how urgent is it really to act on the levy notice? Mine says "Final Notice - Intent to Levy" and gives me 30 days. I'm trying to decide between finding a local EA or attempting to call the IRS directly. The idea of waiting hours on hold is daunting, but the Claimyr service mentioned above sounds interesting if it actually works. Also, has anyone here actually had their bank account levied? I'm terrified they'll clean out my checking account before I can get this sorted out. We have about $3,000 in there which is basically our rent and grocery money for the month. Thanks everyone for sharing your real experiences - it's so much more helpful than the scary marketing from these tax relief companies.
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Amina Diop
ā¢The Final Notice - Intent to Levy is serious, but you do have that 30-day window to act. Don't panic, but don't wait until the last minute either. During those 30 days, the IRS cannot proceed with the levy, so you have time to get things sorted. I'd recommend trying to contact the IRS directly first - either through traditional calling (yes, the wait times are brutal) or using one of those callback services others mentioned. If you can get through, ask for an immediate hold on collection activities while you work out a payment plan. This buys you more time and stops the levy process. Bank levies do happen, but usually the IRS will start with income/wage garnishments first since they're easier to process. Still, protect that $3,000 by acting within your 30-day window. A few quick steps you can take right now: 1. Gather all your tax documents and financial information 2. Calculate what you can realistically pay monthly 3. Consider requesting an installment agreement online through IRS.gov if your situation is straightforward 4. If it's complex, find a local EA but don't pay the huge upfront fees these national companies want You've got this - just don't let the fear paralyze you into inaction during your 30-day window.
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